Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200541X/om6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680200541X/om6085Isup2.hkl |
CCDC reference: 185736
Crystals of (I) were grown by slow evaporation of a solution containing 0.1 M NaMES (pH 6.0) and 40% methyl pentanediol (MPD). The data crystal was cleaved from a larger plate.
All H atoms were located in the difference map. Coordinates and isotropic displacement parameters were refined for the H atoms on the solvent (water) molecule. All other H atoms were refined using the riding model.
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I) showing the water molecule bound to the N atom. Displacement ellipsoids are shown at the 50% probability level. |
Na+·C6H12NO4S−·H2O | Dx = 1.532 Mg m−3 |
Mr = 235.23 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 5332 reflections |
a = 6.3673 (5) Å | θ = 2.9–28.3° |
b = 11.3245 (9) Å | µ = 0.36 mm−1 |
c = 28.297 (2) Å | T = 93 K |
V = 2040.4 (3) Å3 | Prism, colorless |
Z = 8 | 0.40 × 0.40 × 0.20 mm |
F(000) = 992 |
Bruker SMART1000 CCD diffractometer | 2516 independent reflections |
Radiation source: sealed tube | 2272 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −8→8 |
Tmin = 0.833, Tmax = 0.943 | k = −15→14 |
14538 measured reflections | l = −35→37 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0405P)2 + 1.6377P] where P = (Fo2 + 2Fc2)/3 |
2516 reflections | (Δ/σ)max = 0.001 |
135 parameters | Δρmax = 0.46 e Å−3 |
2 restraints | Δρmin = −0.36 e Å−3 |
Na+·C6H12NO4S−·H2O | V = 2040.4 (3) Å3 |
Mr = 235.23 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 6.3673 (5) Å | µ = 0.36 mm−1 |
b = 11.3245 (9) Å | T = 93 K |
c = 28.297 (2) Å | 0.40 × 0.40 × 0.20 mm |
Bruker SMART1000 CCD diffractometer | 2516 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2272 reflections with I > 2σ(I) |
Tmin = 0.833, Tmax = 0.943 | Rint = 0.027 |
14538 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 2 restraints |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.46 e Å−3 |
2516 reflections | Δρmin = −0.36 e Å−3 |
135 parameters |
Experimental. Final cell refinement and decay correction applied after integration as part of merge process in SAINT v6.02 A. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Na1 | −0.04058 (9) | 0.13677 (5) | 0.24209 (2) | 0.01324 (15) | |
N1 | 0.5411 (2) | 0.06214 (11) | 0.10008 (4) | 0.0126 (3) | |
C2 | 0.6779 (2) | −0.02585 (14) | 0.07802 (5) | 0.0153 (3) | |
H2A | 0.5955 | −0.0745 | 0.0556 | 0.018* | |
H2B | 0.7365 | −0.0787 | 0.1026 | 0.018* | |
C3 | 0.8546 (3) | 0.03474 (16) | 0.05200 (6) | 0.0213 (3) | |
H3A | 0.9386 | 0.0818 | 0.0746 | 0.026* | |
H3B | 0.9480 | −0.0255 | 0.0378 | 0.026* | |
O4 | 0.77609 (19) | 0.11016 (11) | 0.01573 (4) | 0.0219 (3) | |
C5 | 0.6452 (3) | 0.19790 (14) | 0.03660 (6) | 0.0211 (3) | |
H5A | 0.5898 | 0.2504 | 0.0116 | 0.025* | |
H5B | 0.7299 | 0.2467 | 0.0585 | 0.025* | |
C6 | 0.4635 (2) | 0.14337 (14) | 0.06336 (6) | 0.0169 (3) | |
H6A | 0.3787 | 0.2065 | 0.0782 | 0.020* | |
H6B | 0.3721 | 0.0997 | 0.0411 | 0.020* | |
C7 | 0.3606 (2) | 0.00662 (14) | 0.12326 (5) | 0.0155 (3) | |
H7A | 0.2708 | −0.0308 | 0.0989 | 0.019* | |
H7B | 0.2764 | 0.0684 | 0.1392 | 0.019* | |
C8 | 0.4244 (2) | −0.08635 (13) | 0.15948 (5) | 0.0136 (3) | |
H8A | 0.5488 | −0.0587 | 0.1773 | 0.016* | |
H8B | 0.4622 | −0.1607 | 0.1431 | 0.016* | |
S1 | 0.21366 (5) | −0.11227 (3) | 0.198900 (13) | 0.01066 (11) | |
O1 | 0.26616 (17) | −0.22069 (10) | 0.22390 (4) | 0.0140 (2) | |
O2 | 0.02574 (17) | −0.12316 (10) | 0.16982 (4) | 0.0163 (2) | |
O3 | 0.20724 (16) | −0.00894 (9) | 0.22975 (4) | 0.0145 (2) | |
O1S | −0.20766 (19) | −0.32879 (11) | 0.18371 (4) | 0.0186 (3) | |
H1S | −0.172 (4) | −0.359 (2) | 0.1570 (7) | 0.039 (7)* | |
H2S | −0.159 (4) | −0.2619 (16) | 0.1813 (8) | 0.039 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Na1 | 0.0082 (3) | 0.0126 (3) | 0.0189 (3) | 0.0006 (2) | 0.0005 (2) | −0.0005 (2) |
N1 | 0.0111 (6) | 0.0126 (6) | 0.0142 (6) | 0.0010 (5) | 0.0016 (5) | 0.0013 (5) |
C2 | 0.0156 (7) | 0.0161 (7) | 0.0142 (7) | 0.0031 (6) | 0.0025 (5) | 0.0000 (5) |
C3 | 0.0156 (8) | 0.0260 (8) | 0.0221 (8) | 0.0042 (7) | 0.0048 (6) | 0.0053 (6) |
O4 | 0.0204 (6) | 0.0247 (6) | 0.0208 (6) | 0.0034 (5) | 0.0064 (5) | 0.0065 (5) |
C5 | 0.0211 (8) | 0.0161 (7) | 0.0261 (8) | −0.0009 (6) | 0.0041 (7) | 0.0047 (6) |
C6 | 0.0146 (8) | 0.0172 (7) | 0.0190 (7) | 0.0030 (6) | 0.0023 (6) | 0.0046 (6) |
C7 | 0.0101 (7) | 0.0201 (7) | 0.0164 (7) | 0.0014 (6) | 0.0015 (5) | 0.0048 (6) |
C8 | 0.0106 (7) | 0.0145 (7) | 0.0156 (7) | 0.0011 (5) | 0.0023 (5) | 0.0023 (5) |
S1 | 0.00779 (18) | 0.00962 (17) | 0.01455 (18) | −0.00004 (12) | 0.00029 (12) | 0.00116 (12) |
O1 | 0.0112 (5) | 0.0126 (5) | 0.0183 (5) | 0.0011 (4) | 0.0009 (4) | 0.0037 (4) |
O2 | 0.0104 (5) | 0.0184 (5) | 0.0200 (5) | −0.0028 (4) | −0.0038 (4) | 0.0031 (4) |
O3 | 0.0116 (5) | 0.0124 (5) | 0.0196 (5) | 0.0006 (4) | 0.0013 (4) | −0.0026 (4) |
O1S | 0.0208 (6) | 0.0153 (5) | 0.0197 (6) | −0.0040 (5) | 0.0060 (5) | −0.0035 (5) |
Na1—O3 | 2.3096 (12) | C5—C6 | 1.515 (2) |
Na1—O1Si | 2.3347 (13) | C5—H5A | 0.9900 |
Na1—O1Sii | 2.6569 (14) | C5—H5B | 0.9900 |
Na1—O1ii | 2.3655 (12) | C6—H6A | 0.9900 |
Na1—O1iii | 2.4339 (12) | C6—H6B | 0.9900 |
Na1—O3iv | 2.4364 (12) | C7—C8 | 1.524 (2) |
Na1—Na1v | 3.2150 (3) | C7—H7A | 0.9900 |
N1—C2 | 1.4635 (19) | C7—H7B | 0.9900 |
N1—C7 | 1.4648 (19) | C8—S1 | 1.7695 (15) |
N1—C6 | 1.4732 (19) | C8—H8A | 0.9900 |
C2—C3 | 1.510 (2) | C8—H8B | 0.9900 |
C2—H2A | 0.9900 | S1—O1 | 1.4558 (11) |
C2—H2B | 0.9900 | S1—O2 | 1.4574 (11) |
C3—O4 | 1.426 (2) | S1—O3 | 1.4606 (11) |
C3—H3A | 0.9900 | O1S—H1S | 0.858 (16) |
C3—H3B | 0.9900 | O1S—H2S | 0.822 (16) |
O4—C5 | 1.425 (2) | ||
O3—Na1—O1Si | 118.79 (5) | N1—C2—H2A | 109.7 |
O3—Na1—O1ii | 164.55 (5) | C3—C2—H2A | 109.7 |
O1Si—Na1—O1ii | 75.94 (4) | N1—C2—H2B | 109.7 |
O3—Na1—O1iii | 87.21 (4) | C3—C2—H2B | 109.7 |
O1Si—Na1—O1iii | 103.44 (5) | H2A—C2—H2B | 108.2 |
O1ii—Na1—O1iii | 93.98 (5) | O4—C3—C2 | 111.21 (14) |
O3—Na1—O3iv | 90.91 (4) | O4—C3—H3A | 109.4 |
O1Si—Na1—O3iv | 83.80 (4) | C2—C3—H3A | 109.4 |
O1ii—Na1—O3iv | 85.92 (4) | O4—C3—H3B | 109.4 |
O1iii—Na1—O3iv | 172.52 (5) | C2—C3—H3B | 109.4 |
O3—Na1—O1Sii | 79.51 (4) | H3A—C3—H3B | 108.0 |
O1Si—Na1—O1Sii | 160.58 (6) | C5—O4—C3 | 108.95 (13) |
O1ii—Na1—O1Sii | 86.53 (4) | O4—C5—C6 | 111.69 (13) |
O1iii—Na1—O1Sii | 69.06 (4) | O4—C5—H5A | 109.3 |
O3iv—Na1—O1Sii | 103.48 (4) | C6—C5—H5A | 109.3 |
O3—Na1—Na1v | 49.04 (3) | O4—C5—H5B | 109.3 |
O1Si—Na1—Na1v | 141.12 (4) | C6—C5—H5B | 109.3 |
O1ii—Na1—Na1v | 123.00 (3) | H5A—C5—H5B | 107.9 |
O1iii—Na1—Na1v | 47.04 (3) | N1—C6—C5 | 110.54 (13) |
O3iv—Na1—Na1v | 127.38 (3) | N1—C6—H6A | 109.5 |
O1Sii—Na1—Na1v | 45.64 (3) | C5—C6—H6A | 109.5 |
O3—Na1—Na1iv | 134.23 (3) | N1—C6—H6B | 109.5 |
O1Si—Na1—Na1iv | 54.45 (3) | C5—C6—H6B | 109.5 |
O1ii—Na1—Na1iv | 48.85 (3) | H6A—C6—H6B | 108.1 |
O1iii—Na1—Na1iv | 137.76 (3) | N1—C7—C8 | 112.87 (12) |
O3iv—Na1—Na1iv | 45.72 (3) | N1—C7—H7A | 109.0 |
O1Sii—Na1—Na1iv | 118.62 (4) | C8—C7—H7A | 109.0 |
Na1v—Na1—Na1iv | 163.99 (4) | N1—C7—H7B | 109.0 |
S1—O1—Na1vi | 129.33 (6) | C8—C7—H7B | 109.0 |
S1—O1—Na1vii | 145.78 (7) | H7A—C7—H7B | 107.8 |
Na1vi—O1—Na1vii | 84.10 (4) | C7—C8—S1 | 109.66 (10) |
S1—O3—Na1 | 132.99 (7) | C7—C8—H8A | 109.7 |
S1—O3—Na1v | 136.03 (6) | S1—C8—H8A | 109.7 |
Na1—O3—Na1v | 85.24 (4) | C7—C8—H8B | 109.7 |
Na1viii—O1S—Na1vi | 79.91 (4) | S1—C8—H8B | 109.7 |
Na1viii—O1S—H1S | 137.8 (18) | H8A—C8—H8B | 108.2 |
Na1vi—O1S—H1S | 118.6 (17) | O1—S1—O2 | 113.05 (6) |
Na1viii—O1S—H2S | 118.3 (17) | O1—S1—O3 | 113.06 (7) |
Na1vi—O1S—H2S | 88.6 (17) | O2—S1—O3 | 112.48 (6) |
C2—N1—C7 | 111.46 (12) | O1—S1—C8 | 105.79 (7) |
C2—N1—C6 | 108.91 (12) | O2—S1—C8 | 106.30 (7) |
C7—N1—C6 | 108.70 (12) | O3—S1—C8 | 105.38 (7) |
N1—C2—C3 | 110.02 (13) | H1S—O1S—H2S | 101 (2) |
Symmetry codes: (i) −x−1/2, y+1/2, z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1/2, y+1/2, z; (iv) x−1/2, y, −z+1/2; (v) x+1/2, y, −z+1/2; (vi) −x, y−1/2, −z+1/2; (vii) −x+1/2, y−1/2, z; (viii) −x−1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1S—H1S···N1vii | 0.86 (2) | 2.02 (2) | 2.8724 (17) | 170 (2) |
O1S—H2S···O2 | 0.82 (2) | 1.99 (2) | 2.7902 (16) | 165 (2) |
Symmetry code: (vii) −x+1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | Na+·C6H12NO4S−·H2O |
Mr | 235.23 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 93 |
a, b, c (Å) | 6.3673 (5), 11.3245 (9), 28.297 (2) |
V (Å3) | 2040.4 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.833, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14538, 2516, 2272 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.089, 1.12 |
No. of reflections | 2516 |
No. of parameters | 135 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.36 |
Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1S—H1S···N1i | 0.858 (16) | 2.023 (17) | 2.8724 (17) | 170 (2) |
O1S—H2S···O2 | 0.822 (16) | 1.988 (17) | 2.7902 (16) | 165 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
In this study, we report the results of a structural study on a sodium salt of 2-(N-morpholino)ethanesulfonate (MES), (I). MES crystallized as a monohydrate of the sodium salt in the orthorhombic space group Pbca, with one molecule of MES, one sodium cation and one water molecule in the asymmetric unit. Low-temperature data (93 K) allowed refinement of the position of the solvent H atoms. The water molecule acts as a donor in hydrogen bonds to N1 and a sulfur O atom (O2).
The structure of a monohydrate of 2-(N-morpholino)ethanesulfonic acid was previously reported (Christensen et al., 1993). Comparing the results of the present study with the previously published room-temperature study results in an r.m.s. deviation of 0.098 Å for all atoms (except the sulfur O atoms) in the sulfonic acid.
Good buffers are commonly used in biochemistry and biology based on their relatively inert behavior with regard to affecting cell functions (Good et al., 1966; Good & Izawa, 1972; Ferguson et al., 1980). Some studies require a knowledge of diffusion coefficients in order to properly interpret the results from an experiment. Diffusion coefficients can be estimated from the Stokes radius (Kunkel, 2000). Lacking the results from a three-dimensional structural study, Kunkel (2000) used a molecular model and estimated the Stokes radius to be 3.54 Å. This resulted in an estimated diffusion coefficient of 0.820 (expressed as D × 105/cm2 sec-1). Applying the method of Kunkel to the results from this study yields a Stokes radius of 4.18 Å (using the distance from O1 to H5A) and a corresponding diffusion coefficient of 0.744. This is in good agreement with the results from the previous X-ray study (i.e. Stokes radius of 4.15 Å for O1 to H13 and a diffusion coefficient of 0.744). The large difference in the estimated Stokes radius (3.54 Å) and those derived from X-ray studies (4.18 and 4.15 Å) translates to an error of approximately 10% in the diffusion coefficient.